JPH0257526B2 - - Google Patents
Info
- Publication number
- JPH0257526B2 JPH0257526B2 JP62075914A JP7591487A JPH0257526B2 JP H0257526 B2 JPH0257526 B2 JP H0257526B2 JP 62075914 A JP62075914 A JP 62075914A JP 7591487 A JP7591487 A JP 7591487A JP H0257526 B2 JPH0257526 B2 JP H0257526B2
- Authority
- JP
- Japan
- Prior art keywords
- macrocyclic
- ketone
- macrocyclic ketone
- light
- cyclopentadecanone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002576 ketones Chemical class 0.000 claims description 35
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 125000005594 diketone group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 6
- 238000006657 acyloin condensation reaction Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000005690 diesters Chemical class 0.000 claims description 5
- 230000001678 irradiating effect Effects 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 3
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- VZAZWURAKYCTAG-UHFFFAOYSA-N cyclopentadecane-1,2-dione Chemical compound O=C1CCCCCCCCCCCCCC1=O VZAZWURAKYCTAG-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000001953 sensory effect Effects 0.000 description 3
- MWKAGZWJHCTVJY-UHFFFAOYSA-N 3-hydroxyoctadecan-2-one Chemical compound CCCCCCCCCCCCCCCC(O)C(C)=O MWKAGZWJHCTVJY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000003997 cyclic ketones Chemical class 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62075914A JPS63243049A (ja) | 1987-03-31 | 1987-03-31 | 大環状ケトンの精製方法 |
| DE88302784T DE3882561T2 (de) | 1987-03-31 | 1988-03-29 | Verfahren zur Reinigung von makrozyklischen Ketonen. |
| EP88302784A EP0285372B1 (en) | 1987-03-31 | 1988-03-29 | Method for purifying macrocyclic ketones |
| US07/176,054 US4917783A (en) | 1987-03-31 | 1988-03-31 | Method for purifying macrocyclic ketones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62075914A JPS63243049A (ja) | 1987-03-31 | 1987-03-31 | 大環状ケトンの精製方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63243049A JPS63243049A (ja) | 1988-10-07 |
| JPH0257526B2 true JPH0257526B2 (enrdf_load_stackoverflow) | 1990-12-05 |
Family
ID=13590068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62075914A Granted JPS63243049A (ja) | 1987-03-31 | 1987-03-31 | 大環状ケトンの精製方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4917783A (enrdf_load_stackoverflow) |
| EP (1) | EP0285372B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS63243049A (enrdf_load_stackoverflow) |
| DE (1) | DE3882561T2 (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9715318D0 (en) * | 1997-07-22 | 1997-09-24 | Bp Chem Int Ltd | Decolourisation process |
| DE102005048250A1 (de) * | 2005-10-07 | 2007-04-12 | Basf Ag | Verfahren zur Farbzahlverbesserung |
| CN113504318A (zh) * | 2021-06-23 | 2021-10-15 | 山东宏济堂制药集团股份有限公司 | 环十五烷酮的检测及验证方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB857163A (en) * | 1957-01-19 | 1960-12-29 | Council Scient Ind Res | A process for the preparation of tridecane-1:13-dicarboxylic acid or its ester, suitable for the preparation of exaltone (cyclopentadecanone) |
| US3439056A (en) * | 1967-09-01 | 1969-04-15 | Goodyear Tire & Rubber | Macrocyclic compounds preparation |
| US3975442A (en) * | 1970-12-09 | 1976-08-17 | Hoffmann-La Roche Inc. | 2-Alkyl-2-(3-oxoalkyl)-1,3-cyclopentadiones |
| JPS6156148A (ja) * | 1984-08-28 | 1986-03-20 | Nippon Mining Co Ltd | 大環状ケトンを製造する方法 |
| JPS6156145A (ja) * | 1984-08-28 | 1986-03-20 | Nippon Mining Co Ltd | 大環状ケトンを製造する法 |
| JPS6156147A (ja) * | 1984-08-28 | 1986-03-20 | Nippon Mining Co Ltd | 大環状ケトンの製造法 |
| JPS6156146A (ja) * | 1984-08-28 | 1986-03-20 | Nippon Mining Co Ltd | 大環状ケトンの製造方法 |
| JPS62190140A (ja) * | 1986-02-14 | 1987-08-20 | Nippon Mining Co Ltd | 大環状ケトンの製造方法 |
-
1987
- 1987-03-31 JP JP62075914A patent/JPS63243049A/ja active Granted
-
1988
- 1988-03-29 DE DE88302784T patent/DE3882561T2/de not_active Expired - Lifetime
- 1988-03-29 EP EP88302784A patent/EP0285372B1/en not_active Expired - Lifetime
- 1988-03-31 US US07/176,054 patent/US4917783A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0285372A3 (en) | 1990-04-25 |
| JPS63243049A (ja) | 1988-10-07 |
| US4917783A (en) | 1990-04-17 |
| DE3882561T2 (de) | 1993-11-18 |
| EP0285372A2 (en) | 1988-10-05 |
| EP0285372B1 (en) | 1993-07-28 |
| DE3882561D1 (de) | 1993-09-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK149345B (da) | Fremgangsmaade til fremstilling af d,l-vincamin eller d,l-isovincamin eller de optiske antipoder deraf | |
| Marshall et al. | Stereoselective synthesis of. alpha.-and. beta.-agarofuran | |
| Huie et al. | Facile one-step synthesis of phenyl-tert-butylnitrone (PBN) and its derivatives | |
| JPH0257526B2 (enrdf_load_stackoverflow) | ||
| EP0001733B1 (fr) | 5-Méthoxy-psoralène comme nouveau médicament et procédé de synthèse | |
| JP3159990B2 (ja) | 香料成分としてのフラノンの使用 | |
| JP2003292488A (ja) | ポリメトキシフラボン類の分離方法 | |
| US5114915A (en) | Decalin ketones, their use in perfumery and process for the preparation thereof | |
| US4335261A (en) | Process for purifying macrocyclic ketones | |
| JPH0515697B2 (enrdf_load_stackoverflow) | ||
| Zderic et al. | Sapogenins. XLI. 1 A New Reaction of the Spiroketal Side Chain | |
| JPH10182549A (ja) | アルケニルサリチル酸の分離精製方法 | |
| FR2468605A1 (fr) | Procede de preparation d'ester de l'acide apovincaminique | |
| Smissman et al. | Baeyer-Villiger Oxidation of α-Substituted Ketones1 | |
| Schuetz et al. | Total synthesis of (.+-.)-1-deaza-1-thiareserpine | |
| Chaumont-Olive et al. | Synthesis of β-damascone from 2, 6-dimethylcyclohexanone | |
| Newman et al. | The synthesis of 2-methyl-3, 4-benzphenanthrene | |
| RU2168491C1 (ru) | Способ выделения диэтилового эфира | |
| Rowland et al. | Saponification of dimethyl cis-2, 6-diphenyl-4-oxocyclohexane-1, 1-dicarboxylate. A reinvestigation | |
| JP2547644B2 (ja) | 新規物質Ｆｒー１２、Ｆｒ１４ーＡ及びその製造法並びにそれを有効成分とする抗酸化剤 | |
| EP0000679B1 (fr) | Nouveau procédé de préparation de la glafénine | |
| RU2036962C1 (ru) | Способ получения душистого вещества, обладающего амбровым запахом, из склареола | |
| Dennis et al. | Photochemical products of trans-Cinnamic alcohol: Possible formation of skin irritants and allergens | |
| JPH0155259B2 (enrdf_load_stackoverflow) | ||
| Myhre et al. | Adducts of Mesitaldehyde and Strong Molecular Acids |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
| R371 | Transfer withdrawn |
Free format text: JAPANESE INTERMEDIATE CODE: R371 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| LAPS | Cancellation because of no payment of annual fees |